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Jon B., prior to his rise to fame, used to be a songwriter and wrote songs for After 7, Toni Braxton, Michael Jackson, Color Me Badd and others. Jon B.'s popularity began in the 90's, he released his debut studio album in 1995 entitled Bonafide; the album spawned the popular hit and Grammy-nominated single "Someone to Love", which featured the Grammy Award-winning artist Babyface. The album was a commercial success as it went platinum, selling over 1 million copies.

Jon's fame began to increase after the release of his first commercially successful debut album Bonafide. He released his second studio album Cool Relax in 1997, the album spawned the top 10 single "They Don't Know" and two other top 20 hits, one featuring Tupac Shakur. Cool Relax received generally positive reviews from music critics and it is his most successful album commercially, it has been certified as Double Platinum by the RIAA.

While on tour promoting Cool Relax, he formed a group with two of his back-up singers, Dominiquinn and Silky Deluxe, named Jack Herrera collectively.[2] A full album, titled Retro Futuristo, was put together, but never officially released. However, two tracks from the project did see release. "Free to Believe" appeared on the soundtrack to the film Light It Up and "High Off You" appeared on Red Star Sounds, Vol. 1: Soul Searching.